This research reports the initial findings of a statewide study that looks at health, insurance, and access to health care among families leaving Temporary Assistance to Needy Families (TANF) for work. Most national and state-level evaluation projects focus primarily on the employment characteristics of TANF leavers and pay little or no attention to health and access to health care. The quantitative data are from a sample of 637 adults in Oregon leaving TANF for work, and they are personalized by qualitative data from a subsample of 90 respondents. Our findings reveal significant barriers to accessing the health care system, even at a time when Medicaid enrollment is considered automatic, in a state with a relatively generous expanded Medicaid program.